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- Title
Carbodiimide and Isocyanate Hydroboration by a Cyclic Carbodiphosphorane Catalyst**.
- Authors
Janda, Ben A.; Tran, Julie A.; Chang, Daniel K.; Nerhood, Gabriela C.; Maduka Ogba, O.; Liberman‐Martin, Allegra L.
- Abstract
We report hydroboration of carbodiimide and isocyanate substrates catalyzed by a cyclic carbodiphosphorane catalyst. The cyclic carbodiphosphorane outperformed the other Lewis basic carbon species tested, including other zerovalent carbon compounds, phosphorus ylides, an N‐heterocyclic carbene, and an N‐heterocyclic olefin. Hydroborations of seven carbodiimides and nine isocyanates were performed at room temperature to form N‐boryl formamidine and N‐boryl formamide products. Intermolecular competition experiments demonstrated the selective hydroboration of alkyl isocyanates over carbodiimide and ketone substrates. DFT calculations support a proposed mechanism involving activation of pinacolborane by the carbodiphosphorane catalyst, followed by hydride transfer and B−N bond formation.
- Subjects
ISOCYANATES; HYDROBORATION; CARBON compounds; KETONES; FORMAMIDINES; YLIDES; ALKENES
- Publication
Chemistry - A European Journal, 2024, Vol 30, Issue 3, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202303095